


Flashbacks

by bringmesomepie



Series: Dean and Cas Modern Life [20]
Category: Supernatural
Genre: 50 bucks, BAMF Mary, Deals, F/M, Flashback, Gen, M/M, Mpreg, Sam is bad at making bets, Spring Fling, The Beginning, Wyatt - Freeform, non-graphic birth, plus six months of laundry, surprise
Language: English
Status: Completed
Published: 2014-04-25
Updated: 2014-04-25
Packaged: 2018-01-20 17:23:05
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,189
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1518944
Author URL: https://archiveofourown.org/users/bringmesomepie/pseuds/bringmesomepie
Summary: <blockquote class="userstuff">
              <p>“Alright, 40 bucks plus I’ll do your laundry for a whole month.” Sam smirked. “If you lose you own me 40 bucks plus the laundry.”</p><p>“Make it 6 months and 50 bucks and it’s a deal.”</p>
            </blockquote>





	Flashbacks

**Author's Note:**

> sorry about the long wait, i couldn't think of anything to write about so i decided to add a chapter about how Wyatt came to be because i have only written a few blurps of how Dean got pregnant with Wyatt. I will go back to the actual plot line soon, i just felt like i need to update this series with a little flashback... :D

“Come on, Sam! Jess, Jo, and Cas are already there.” Dean hurried out of the house.

“Slow down, Dean. We aren’t going to get there any faster.” Sam smiled. “Who are you gonna hook up with?”

Dean gasped. “You actually think I’m that low to hook up with one of my friends?”

“Well, Chuck, Cassie, Gabe, and Alfie are going to be joining us shortly.”

“Well, when we get there we can relax and get wasted.” Dean smiled starting the car.

“We aren’t even old enough to drink, Dean.” Sam retorted.

“Well, it’s spring break, and we are spending it with our friends in a cabin far away from our folks. A few beers and maybe a few shots never hurt anybody. Don’t tell me you don’t want to get in Jess’s pants.”

“Shut up.” Sam’s face turned fiery red.

“Oh, Sammy. You sly dog.” Dean laughed.

“I said shut up.” Sam laughed. “I bet you can’t go the whole trip without sleeping with one of the girls.”

“How much?”

“40 bucks.” Sam crossed his arms over his chest.

Dean snorted. “40 bucks? Only 40 bucks to go with sex with a house full of girls for 2 weeks. Yeah, right.”

“Alright, 40 bucks plus I’ll do your laundry for a whole month.” Sam smirked. “If you lose you own me 40 bucks plus the laundry.”

“Make it 6 months and 50 bucks and it’s a deal.”

“Fine.” Sam stretched out his hands and Dean grabbed it and they shook on it. “Deal.”

&^%$#@!@#$%^&*&^%$#@!@#$%^&*

“Come on, Sam. One beer.” Dean begged with Jo. “Most 16 year olds would definitely be accepting a beer.”

“Stop, Dean. I don’t want to. I have other plans.”

“Your right hand doesn’t count.” Jo replied before Dean could.

“No, I have plans with Jess.” Sam said.

“Come on, Jo. Cas and Anna are meeting us at the bar.” Dean smirked.

*&^%$#@!@#^&*&^%$#@!@#$%^&*

“You’re sucka dork, Sam Winchester.” Jess laughed as they sat down on the couch of the basement Sam, Jess, Gabe, and Alfie were sharing with a pull out couch and four cots.

“How? It was just a little bet.”

“Yeah, but you know Dean. He will do anything to find a loop hole in your deal.”

“How? This one is fool proof. The deal was Dean couldn’t have sex with any of the girls during this trip.”

“That deal is almost as stupid and cruel as the bet you made with Dean when he got the violent stomach bug on the way home from the Grand Crayon last summer.”

“Oh yeah, the bet that Dean wouldn’t puke the whole car trip.” Sam smiled.

“Oh, but do you remember the ending.” Jess poked. Sam’s smiled faded. “Right as we all got to your house Dean puked in your lap.”

“Yeah, Cas still blames me for messing up his car.”

“You are going to regret making that deal, I know it. You always do.” Jess shook her head.

Sam smiled and stared into Jess’s eyes. “Hey, Jess, I have been meaning to ask you…”

“Yes, Sam, I feel the same as you do.” Jess smiled not letting Sam finished.

“How---“

“I have been your best friend since 6th grade, I know a thing or two about you.” Jess smiled and crawled closer to Sam. Sam leaned in and pressed his lips into Jess’s.

It was a quick peck but Sam definitely felt the fireworks. Jess let out a breath of air. “That was…”

“Great…”

“Yeah, what you said.” Jess smirked as they heard rustling from upstairs. “I guess some people are home.”

“Yeah, wanna go see if they need help?” Sam started to stand when Jess grabbed his arm.

“Let’s wait until it quiet’s down.” Jess said listening closely.

After ten minutes they walked upstairs to find a trail of clothes leading to Dean’s room. “I knew Dean couldn’t keep the deal.” Sam smiled. Jess stared at the ground.

“Sam, I don’t know about that. I mean, look. Here is definitely Dean’s shirt and pants.” Jess walked towards the front door. “This is Dean’s leather jacket but who all do we know that wearing a trench coat? There’s also two pairs of guys boots on the floor.”

“ _Dammit_ , Dean.” Sam moaned. Jess laughed and walked over to Sam.

“How is it that Dean always seems to find a loophole in your deals?”

“Shut up, Sam walked back down to the basement.

&^%$#@!@#$^&*&^%$#@

Dean woke up surprisingly not hung over. He rolled over to realize that he was being spooned by no one other than his best friend Cas. Cas was as wide eyed as Dean was. He both sat up and look at each other. “Did we?” Cas managed to say.

“I think we did.”

“Did I?”

“You did.” Dean looked away from Cas.

“Wha—what does this mean?” Cas asked.

“What do you want this to mean?”

“I don’t know, did you like it?”

“I don’t know how to answer that…”

“Me neither.”

“I think we should give it a shot.” Dean mumbled.

“What?”

“I have feelings for you Cas. I have for a while.”

Cas smiled. “Ok, these give this a shot.”

&^%$#@!@#$^&*&^%$#@!@#$%^&*

Sam pouted the rest of the vacation and the whole ride home. “Sammy, cheer up.” Dean tapped Sam’s shoulder.

“Shut up.” Sam grumbled.

“Why? What did I do?” Dean smiled.

“You fucking found a loophole in the deal and decided to fuck Cas.”

“I was drunk, Sammy. I wasn’t even thinking about that fucking deal. I don’t remember anything from that night. I just woke up being spooned by Cas. We decided to give us a shot.”

“So you’re gay now? Dean Winchester, the sex god, is gay?”

Dean snorted and thought for a moment. “Yep. You got a problem with that, Sammy?”

“No!” Sam remarked loudly.

“Then pipe the fuck down.”

“If I knew that you were gay I would have worded the bet differently.” Sam grumbled pressing his face against the window.

“I didn’t even know I was gay until that night.”

“Whatever.” Sam drifted to sleep.

&^%$#@#$%^I*&^%$#@#$%^&

**_2 Month Later…_ **

“Dean? Honey, are you ok? You’ve been in the bathroom for a while.” Mary asked knocking on the door. Dean slowly opened the door. He was sweaty, pale, and weak. “Oh, sweetie, are you feeling ok?”

“I’m fine, Mom. It’s just a bug or something.” Dean waved Mary away.

“No, you have been sick for weeks and haven’t gotten any better. I have already called Dr. Henrickson and set a appointment for an hour from now.”

“Momm…”

“Don’t Mom me, Dean Michael Winchester. It’s a mother’s right to worry about her children.”

“Yes, m’am.” Dean grumbled to his room.

He got dressed and walked into the kitchen where his mother was waiting. “Are you ready to go?”

“As ready as I’ll ever be.” Dean said walked over to the fridge and grabbing a water bottle. “See ya later, Sammy.”

Dean ruffled Sam’s hair. “Stop, Dean.”

Dean laughed and walked outside with Mary. “Why can’t I drive myself to the doctor, Mom?”

“Because I don’t trust you actually going there and you should be driving and sick.” Mom got into the Driver’s seat of Dean’s beloved Impala.

45 minutes later Dean was sitting on the paper cover bed in a paper, backless cover-up with his mom sitting in the chair next to him.

There was a knock on the door and a middle age man entered the room. “Hello, Mr. Winchester.”

“Dean, Mr. Winchester is my father.” That got a glare from Mary.

“I’m your doctor, Dr. Henrickson.” The man held out his hand towards Dean. Dean hesitated but took the man’s hand.

“Have you gotten the blood test back?” Mary asked before Dr. Henrickson sat down.

He laughed. “Mrs. Winchester, you don’t need to worry, everything fine with Dean.” Mary let out a sigh of relief, but Dean knew there was a but in there.

“What’s the catch?” Dean blurted out.

“Dean—“ Mary scolded glaring at her eldest.

“It’s ok, Mrs. Winchester. Dean was correct there is a catch.” He looked at Dean and opened the manila folder. “We did a couple test on Dean’s blood work and they all came back positive that Dean’s pregnant.”

Mary’s hands went straight up to her mouth with a gasp and Dean’s spine straightened and eyes went wide. “Excuse me?”

“You’re pregnant, Dean.” Dr. Henrickson repeated. “We have a nurse beginning in a sonogram machine right now to determine the age of the fetus.”

5 minutes later the lights were dimmed and Dean was laying on his back while Dr. Henrickson squeezed cold gel on his stomach. Dean took his mother’s hand, exactly glad his mom came because he wouldn’t have been able to handle the on his own. It took a few moment of searching but Dr. Henrickson stop the wand right under Dean’s belly button. “There you go, there’s your baby.”

Dean’s breath hitched which got his mom to squeeze his hand tighter. “Mom—“

“I know, sweetie.”

“It’s seems to me that your baby is around 8 weeks.”

“Thanks, doc.” Dean managed to say as Dr. Henrickson wiped the gel off his stomach. “Wh-when the due date be?”

“I’d say around the beginning of January.” Dr. Henrikson asked a few question about dates and pulled out his calendar. “I’d say around December 17th.”

Dean nodded as he stood from the table fully clothes having just pulled on his pants taking off the paper thing and tugging on his shirt. “Mom, you and Dr. Henrickson and can go on and talk and schedule the next appointment. I—I need a moment.” Dean sat back down in the chair Mary was sitting in moments ago. He was hit with a wave of nausea and dizziness.

They walked out and Dean sat there with his head in his hands. He took deep breaths and he was good again. He got up and walked down the exit where Mary was patiently waiting for him. They walked to the Impala in silence. Dean crawled into the passenger seat as Mary got into with on driver’s side. She didn’t started the car yet. Dean could felt the knot his throat appear and tear weld up in his eyes. He disappointed his mother. He disappointed his family. He disappointed the Winchester name. He turned his head to look at his mom. She was looking down at her hands. “Mom?” Dean voice cracked.

She looked over at him and tears left his tear ducts. “I’m sorry.” Dean choked out. “I’m sorry, I disappointed you.”

Mary quickly slid over to her son and wrapped her arms around him. “No, shhh, don’t cry, sweetheart. I’m not disappointed.”

“I let you down, I had sex with Castiel and hid that from you and now this is my consequence.”

Mary pulled Dean away from her and held his shoulder sternly. “Dean, honey, I’m not mad or disappointed. You didn’t let me down. You’re 19 and in college. So me and your father are going to be grandparents a little earlier than we expected but I’m ok with that.” Mary smiled. “Don’t ever tell me that that baby in there is a consequence. That baby is a gift.”

Dean nodded and they went home. Dean ended up calling Cas later that evening. Cas came over and Dean let the cat out of the bag and Cas was shocked, bewildered, and excited all at the same time. They decided they wanted to get married.

That’s exactly what they did three months later. It was a small wedding with just close friends and family. Dean was only 5 months along so he could still pretty much hide his belly if he wanted.

&^%$#@!@#$%^&^%$#@#$%^&

**_6 Months Later…_ **

“Ow, Come on, Rocket, give me a break.” Dean grumbled as he sat down at the kitchen table where Sam was doing homework. Sam snickered. “What’s so funny?”

“You. You’re talking to something that either won’t listen to you, doesn’t care or can’t hear you.”

“Shut up, bitch.” Dean barked then hissing again and rubbed his belly.

“Jerk.” Sam looked up. “Dean, why are you and Cas living here and not finding a house or apartment somewhere?”

Dean sat back in his chair. “Money’s tight at the moment. Mom and Dad offered to let us stay until we got on our feet after Rocket arrives.” Dean rubbed his belly.

“Is Cas working until late tonight?” Sam asked putting away the last of his homework. “Dad’s gone until tomorrow.”

“Uh, Cas has work until 7.” Dean paused to hiss in pain. “He has a night class at 7:30 til around 11.”

“Dean, are you ok?”

“Yeah.” Dean groaned for a second. “Rocket is just kicking hard.”

“Well, have you finished the nursery yet?”

“Yeah, me and Mom put up the last of it this morning.” Dean put both hands on his belly as if a gesture to dull the pain. “Sammy, what’s today’s date?”

Sam got up and looked at the calendar on the fridge. “Uh, November 19th. Why?”

Dean sat forward and felt a trickle of liquid travel from inside his legs forming a puddle under the chair. “My water just broke.”

Sam’s eyes went wide. “Ok. Um, you go change into some clean clothes and go rest on the couch and I’ll get Mom and call Cas and Dad.”

Dean nodded and followed Sam upstairs. 15 minutes later Dean is sitting wide legged on the couch with Mary sitting on the coffee table coaching Dean. “You’re doing good, Dean. Just breath. Once Sammy gets done packing your bag and Castiel gets home we will leave.”

“Argh…Mom, this hurts. This really hurts.” Dean whimpered taking his mother’s hand and held his stomach.

“I know, baby. They are a good 10 minutes apart. We still have plenty of time.”

Dean relaxed and leaned back on the couch and closed his eyes. This was nothing a 19 year old should have to experience yet. “I don’t wanna do this anymore, Mom.”

Mom smirked. “It’s too late to say that now, pumpkin.”

30 minutes later Cas came flying through the door. “Dean?”

“We’re in the living room.” Mary called out. Cas jogged into the living room and saw Dean walked around the room coated in a thin layer of sweat.

“Hey, baby.” Cas smiled.

“Can we go now” Dean pleaded walking over to Cas.

“How far apart are the contractions?” Cas asked taking Dean’s hand.

“A solid 8 minutes.” Mary smiled. “Sammy, we are going, come on.”

Sam held Dean’s overnight bag as they headed for the car. Sam slid in the passenger seat of his mother car and Mom drove. Cas helped Dean into the back seat. Right as Dean sat down a contraction crashed into him. “Argh!” Dean groaned gripping Cas’s hand tight and the handle bar above the door.

“Just breathe, Dean.”

Dean closed his eyes until the pain seized. He slide the rest of the way in and Cas ran to the other side and they were off. Dean propped against Cas the whole ride. It was a short 15 minute drive to the hospital. “Dean, Dad said he was going to come to the hospital as quick as he could.” Sam announced.

“Great, Sammy.” Dean panted after ending his most recent contraction halfway through the drive.

“They’ve hit 7 minutes.” Mary smirked.

Right as they entered the parking lot of the hospital Dean has a contraction. He grabs Cas thigh and leans forward place his face against the back of the passenger seat and groans. Mary pulled to the overhang at the entrance to the hospital and Sam got out and helped out Dean when the contraction stopped.

Sam had called saying that Dean was in labor and they need a room. Dean was able to walk with Sam to the front desk. The lady at the front desk was in a good mood. Sam smiled. “Hi, I’m Sam Winchester and this is my brother, Dean. I called a few minutes ago.”

“Yeah, I’m in labor.” Dean added unnecessarily.

“Yes, yes, we are getting the room ready right now. A nurse in a few minutes will cal you an wheel you up.”

“No, I can walk perfectly fine.” Dean retorted.

“That’s fine, you don’t have to use the chair. It’s just there in case you do.” She smiled.

Dean nodded and walked over to Sam and slowly made his way down into the seat. “How are you feeling at the moment?” Sam asked genuinely.

“Ready to get this baby out.” Dean moaned as a contraction bubbled to the surface.

“I’m right here, Dean.” Sam said taking his brother hand and Dean squeezed like no one’s business until it was gone. He pulled away his hand.

“Thanks, Sammy.” Dean panted.

“Dean Winchester?” A nurse asked pushing a wheelchair in front of her.

“That’ll be me.” Dean smiled as Cas and Mary walked into the building. Cas raced over to Dean with Mary not too far behind. “Is there anyway I can walk if or until I need the chair?”

“Sure.” She smiled.

*&^%$#@!@#$%^&^%$#@!@#$%^

**_4 Hours Later…_ **

“Argh! God! Mama make it stop.” Dean begged curled in on himself in the bed.

“I’m sorry, hon, there’s nothing I can done unless you want that epidural.” Mary replied. Dean sat up and swung his leg off the side of the bed. A young female doctor walked in.

“Hello, everybody.” She smiled. “You must be Dean.”

“Yeah, who are you?” Dean asked.

“I’m Dr. Rosen. I’ll will be getting you through you delivery.”

“No, where’s Dr. Henrickson?” Dean panicked.

“Dr. Henrickson, unfortunately, passed late night in his sleep, due to a stroke. May he rest in peace. So, I have taken over most of his patients and you, Dean, are one of those.”

Dean walked over to an empty chair and stopped. He didn’t sit he just stood there. “Argh!”

“Alright, Dean, can you come over here and lay down so I can check you out?”

Dean shook his head and squatted down to the ground and pressed his face on the cushioned seat and groaned. “I can’t.”

Dr. Rosen walked over to Dean dan crouched down slightly behind him. “I’m going to check you right here, Dean. Is that ok?”

“Argh! No! Something is pressing down on my insides. I—I—I gotta push.” Dean panted. Cas walked over to Dean and crawled into the chair and sat Indian in the chair. Dean instantly took both of Cas’s hands and pushed.

Without any instructions from Dr. Rosen, Dean deliver a healthy baby boy in two pushes. Once the afterbirth was delivered Dean was back in bed and the infant swaddled in his arms. Cas shared the bed with Dean and the baby boy was in the middle. “What are we gonna name him? He can’t be Rocket forever.”

“I like the first name we picked at the very beginning. Wyatt.”

“How about Wyatt James Winchester?” Cas answered.

“I love it.” Dean smiled down at the baby. “Hey there, little Wyatt. I’m your Daddy and that’s your Papa. You worried us for being so early but we’re glad you’re here.”

                                                                                ***


End file.
